Concise Catalytic Asymmetric Total Synthesis of Biologically Active Tropane Alkaloids

Córdova, Armando; Lin, Shuangzheng; Tseggai, Abrehet

doi:10.1002/adsc.201100917

Cited by 21 publications

(17 citation statements)

References 64 publications

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“…Next, these compounds such as E-6b and 8d can be rapidly converted to tropane alkaloids (e.g., cocaine) [64,65] and secologanine tryptamine alkaloids [67], respectively (Scheme 2b and 2d). An aerobic oxidation/Michael/ carbocyclization cascade sequence employing the combined heterogeneous Pd/chiral amine multiple relay catalysis and molecular oxygen/air as the terminal oxidant was also investigated (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

“…Thus, the palladium (0)-aminopropyl-mesocellular foam (Pd(0)-AmP-MCF)-catalyzed aerobic oxidation [31] of alcohols 1 was linked in sequence with several chiral amine 4 [61]-catalyzed one-pot cascade transformations and provided a variety of functional molecules (e.g., aziridine 3a [62,63], E-6b [64,65], pyrrolidine 7a [66] and 8d [67]) with high enantiomeric ratios (Scheme 2). Next, these compounds such as E-6b and 8d can be rapidly converted to tropane alkaloids (e.g., cocaine) [64,65] and secologanine tryptamine alkaloids [67], respectively (Scheme 2b and 2d).…”

Section: Resultsmentioning

confidence: 99%

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Combined heterogeneous metal/organic catalysts for eco-friendly synthesis

Córdova

2015

Pure and Applied Chemistry

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The interplay and synergistic cooperation between homogeneous and heterogeneous catalyst systems is of utmost importance in nature. It is also applied in chemical synthesis. Here, it can allow for new reactivity, which is not possible by the employment of a single catalyst, and promote the catalysis of multiple transformations in a one-pot sequence. This could overall lead to novel reactions and the development of sustainable chemistry. In this context, a versatile and broad synergistic strategy for the selective synthesis of valuable molecules with variable complexity and under eco-friendly conditions is disclosed. It is based on integrated heterogeneous metal/organo multiple relay catalysis, which is performed in a single reaction vessel, and allows for the assembly of complex molecules (e.g., heterocycles and carbocycles) with up to three quaternary stereocenters in a highly enantioselective fashion from simple alcohols and air/O 2 .

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Combined heterogeneous metal/organic catalysts for eco-friendly synthesis

Córdova

2015

Pure and Applied Chemistry

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“…In 2012, the Córdova group [52] described an excellent total synthesis of the tropane alkaloid (−)-cocaine (Scheme 17), which had been first isolated in 1895 by the Neiman group and exhibits powerful analgesic activity [53]. The group employed a highly enantioselective one-pot aza -Michael/Wittig reaction for the construction of its chiral building block.…”

Section: Asymmetric Total Synthesis Of Bioactive Natural Products mentioning

confidence: 99%

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

Wang

2019

Molecules

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Chirality is one of the most important attributes for its presence in a vast majority of bioactive natural products and pharmaceuticals. Asymmetric organocatalysis methods have emerged as a powerful methodology for the construction of highly enantioenriched structural skeletons of the target molecules. Due to their extensive application of organocatalysis in the total synthesis of bioactive molecules and some of them have been used in the industrial synthesis of drugs have attracted increasing interests from chemists. Among the chiral organocatalysts, chiral secondary amines (MacMillan’s catalyst and Jorgensen’s catalyst) have been especially considered attractive strategies because of their impressive efficiency. Herein, we outline advances in the asymmetric total synthesis of natural products and relevant drugs by using the strategy of chiral secondary amine catalyzed reactions of α,β-unsaturated aldehydes in the last eighteen years.

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“…This compound has been also previously reported. 25 O-THP (TIPS)Propargyl alcohol (20)Compound 20 was prepared according to a modified literature procedure. 26 A solution of compound 18 (1.0 g, 7.1 mmol) in dry THF (20 mL) was cooled to -78°C.…”

Section: Preparation Of Silyl Alkyne Bromidesmentioning

confidence: 99%

An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics

Longin

Langemheen

Liskamp

2017

Bioorganic & Medicinal Chemistry

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The synthesis of a semi-orthogonally protected CycloTriVeratrilene (CTV) scaffold derivative as well as the sequential introduction of three different peptide loops onto this molecular scaffold via Cu(I)-catalyzed azide alkyne cycloaddition towards a medium-sized protein mimic is described. This approach for the construction of medium-sized protein mimics is illustrated by the synthesis of a paratope mimic of the monoclonal antibody Infliximab (Remicade®) and provides access to a range of highly pre-organized molecular constructs bearing three different peptide segments. This approach may find wide applications for development of protein-protein interaction disruptors as well as synthetic vaccines.

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Concise Catalytic Asymmetric Total Synthesis of Biologically Active Tropane Alkaloids

Cited by 21 publications

References 64 publications

Combined heterogeneous metal/organic catalysts for eco-friendly synthesis

Combined heterogeneous metal/organic catalysts for eco-friendly synthesis

Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes

An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics

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